How does KAYAK find such low prices on flights from Hawaii to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Hawaii to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$219 CHEAP FLIGHTS from Hawaii to Chicago

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Cheap Flights from Hawaii to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Hawaii to Chicago

Thu, Aug 27 - Mon, Aug 31

12:59 pm - 5:00 amLIH Lihue-ORD Chicago O'Hare Intl

11h 01m1 stop Los Angeles

6:59 am - 2:55 pmORD Chicago O'Hare Intl-LIH Lihue

12h 56m1 stop Phoenix Sky Harbor Intl

$432American Airlines

Wed, Sep 9 - Sun, Sep 13

9:45 pm - 4:05 pmKOA Kona Intl-ORD Chicago O'Hare Intl

13h 20m1 stop Phoenix Sky Harbor Intl

6:55 am - 4:00 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 05m1 stop Los Angeles

$438American Airlines

Thu, Aug 27 - Mon, Aug 31

9:55 pm - 1:23 pmLIH Lihue-ORD Chicago O'Hare Intl

10h 28m1 stop Seattle/Tacoma Intl

6:00 am - 7:16 pmORD Chicago O'Hare Intl-LIH Lihue

18h 16m2 stops Minneapolis St Paul Seattle/Tacoma Intl

$438Delta

Thu, Aug 27 - Mon, Aug 31

9:55 pm - 6:19 pmLIH Lihue-ORD Chicago O'Hare Intl

15h 24m2 stops Seattle/Tacoma Intl Salt Lake City

6:00 am - 7:16 pmORD Chicago O'Hare Intl-LIH Lihue

18h 16m2 stops Minneapolis St Paul Seattle/Tacoma Intl

$443Delta

Tue, Oct 13 - Tue, Oct 20

7:35 pm - 11:28 amLIH Lihue-ORD Chicago O'Hare Intl

10h 53m1 stop Denver Intl

7:00 am - 3:40 pmORD Chicago O'Hare Intl-LIH Lihue

13h 40m1 stop Denver Intl

$444United Airlines

Fri, Sep 11 - Fri, Sep 18

1:03 pm - 5:42 amLIH Lihue-ORD Chicago O'Hare Intl

11h 39m1 stop Los Angeles

5:00 am - 11:59 amORD Chicago O'Hare Intl-LIH Lihue

11h 59m1 stop San Francisco

$444United Airlines

Sat, Sep 19 - Sat, Sep 26

10:35 am - 1:22 pmKOA Kona Intl-ORD Chicago O'Hare Intl

21h 47m1 stop San Diego

2:18 pm - 2:48 pmORD Chicago O'Hare Intl-KOA Kona Intl

29h 30m1 stop San Diego

$497Alaska Airlines

Mon, Sep 28 - Mon, Oct 5

11:59 pm - 6:05 pmHNL Honolulu-ORD Chicago O'Hare Intl

13h 06m1 stop Los Angeles

7:40 pm - 9:58 amORD Chicago O'Hare Intl-HNL Honolulu

19h 18m2 stops Salt Lake City Los Angeles

$545Multiple Airlines

Thu, Sep 10 - Wed, Sep 16

7:31 am - 11:59 pmHNL Honolulu-ORD Chicago O'Hare Intl

11h 28m1 stop San Diego

3:52 pm - 11:59 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 07m1 stop Seattle/Tacoma Intl

$551Multiple Airlines

Wed, Sep 16 - Wed, Sep 23

7:00 am - 11:59 pmOGG Kahului-ORD Chicago O'Hare Intl

11h 59m1 stop Seattle/Tacoma Intl

2:18 pm - 9:37 pmORD Chicago O'Hare Intl-OGG Kahului

12h 19m1 stop San Diego

$584Alaska Airlines

Recent last minute flight deals from Hawaii to Chicago

Wed, Aug 12 - Tue, Aug 18

7:30 am - 11:36 pmHNL Honolulu-ORD Chicago O'Hare Intl

11h 06m1 stop San Diego

6:20 am - 7:03 pmORD Chicago O'Hare Intl-HNL Honolulu

17h 43m1 stop San Diego

$660Multiple Airlines

Wed, Aug 12 - Tue, Aug 18

7:30 am - 11:36 pmHNL Honolulu-ORD Chicago O'Hare Intl

11h 06m1 stop San Diego

5:42 pm - 12:12 amORD Chicago O'Hare Intl-HNL Honolulu

11h 30m1 stop Seattle/Tacoma Intl

$660Multiple Airlines

Wed, Aug 12 - Tue, Aug 18

7:30 am - 11:36 pmHNL Honolulu-ORD Chicago O'Hare Intl

11h 06m1 stop San Diego

1:01 pm - 9:59 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 58m1 stop Seattle/Tacoma Intl

$715Multiple Airlines

Mon, Aug 10 - Mon, Aug 17

11:55 am - 5:45 amHNL Honolulu-MDW Chicago Midway

12h 50m1 stop Ontario

10:15 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

15h 55m1 stop San Jose

$750Southwest

Mon, Aug 10 - Mon, Aug 17

9:55 pm - 2:45 pmHNL Honolulu-MDW Chicago Midway

11h 50m2 stops San Diego Phoenix Sky Harbor Intl

6:15 am - 12:35 pmMDW Chicago Midway-HNL Honolulu

11h 20m1 stop San Diego

$771Southwest

Thu, Aug 13 - Sat, Aug 22

9:30 pm - 4:59 pmHNL Honolulu-ORD Chicago O'Hare Intl

14h 29m2 stops Los Angeles Minneapolis St Paul

8:28 am - 9:20 pmORD Chicago O'Hare Intl-HNL Honolulu

17h 52m2 stops Minneapolis St Paul Los Angeles

$811Delta

Tue, Aug 11 - Mon, Aug 17

9:45 pm - 2:22 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 37m1 stop Phoenix Sky Harbor Intl

9:00 am - 4:15 pmORD Chicago O'Hare Intl-KOA Kona Intl

12h 15m1 stop Los Angeles

$826American Airlines

Tue, Aug 11 - Mon, Aug 17

8:42 pm - 6:19 pmKOA Kona Intl-ORD Chicago O'Hare Intl

16h 37m2 stops Seattle/Tacoma Intl Salt Lake City

6:00 am - 5:35 pmORD Chicago O'Hare Intl-KOA Kona Intl

16h 35m2 stops Minneapolis St Paul Seattle/Tacoma Intl

$837Delta

Wed, Aug 12 - Tue, Aug 18

1:25 pm - 5:59 amHNL Honolulu-ORD Chicago O'Hare Intl

11h 34m1 stop San Francisco

7:50 pm - 4:25 pmORD Chicago O'Hare Intl-HNL Honolulu

25h 35m2 stops Dallas/Fort Worth San Francisco

$846United Airlines

Wed, Aug 12 - Tue, Aug 18

4:00 pm - 5:04 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 04mnonstop

7:50 pm - 4:25 pmORD Chicago O'Hare Intl-HNL Honolulu

25h 35m2 stops Dallas/Fort Worth San Francisco

$853United Airlines

Useful Info

Low season	January
High season	December
Cheapest flight	$219

Best time to beat the crowds with an average 15% drop in price.

Most popular time to fly and prices are also 16% lower on average.

Flight from Kailua-Kona to Chicago O'Hare Airport

How does KAYAK find such low prices on flights from Hawaii to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Hawaii to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Hawaii

First Class flights to Chicagofrom $6,906

Business Class flights to Chicagofrom $3,490

Premium Economy Class flights to Chicagofrom $2,211

Economy Class flights to Chicagofrom $477

$219 Find Cheap Flights from Hawaii to Chicago - Compare and Save

Cheap Flights from Hawaii to Chicago

Recent round-trip flight deals from Hawaii to Chicago

Recent one-way flight deals from Hawaii to Chicago

Recent last minute flight deals from Hawaii to Chicago

Recent direct flight deals from Hawaii to Chicago

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from Hawaii to Chicago

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Hawaii

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight